Fluorine-substituted 9,9'-dianthracene blue light emitting host material and its application

A blue-light host material, bianthracene technology, applied in the field of blue-light host materials, fluorine-substituted 9,9'-bianthracene blue-light host materials, can solve the difficulty of phosphorescent blue light devices, and it is difficult to achieve high efficiency, good color purity and long-life blue light Devices and blue light devices have poor performance, and achieve the effects of good thermal stability, high fluorescence quantum efficiency, and low turn-on voltage

Active Publication Date: 2014-01-22
西安极光新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the research of OLEDs, the red, green, and blue primary color materials are the basis for realizing full-color display. However, due to the inherent wide band gap of blue light materials, it is difficult to realize high efficiency, good color purity and long life blue light devices.
Therefore, blue devices perform poorly relative to green and red devices
Although phosphorescent electroluminescent devices (PhOLEDs) have been extensively studied, maintaining high efficiency and long lifetime performance is difficult for phosphorescent blue devices.

Method used

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  • Fluorine-substituted 9,9'-dianthracene blue light emitting host material and its application
  • Fluorine-substituted 9,9'-dianthracene blue light emitting host material and its application
  • Fluorine-substituted 9,9'-dianthracene blue light emitting host material and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Synthesis of fluorinated 9,9'-bianthracene blue light material 1:

[0032]

[0033] Under nitrogen atmosphere, to 30mL THF and 10mL, 2.0mol·L –1 K 2 CO 3 In the solution, 10,10′-dibromo-9,9′-bianthracene (2.34mmol), 2-fluorophenylboronic acid (8mmol) and Pd(PPh 3 ) 4 (0.35 mmol). After the reaction, the mixture was heated to reflux for 24h, and the reaction was tracked by point plate. After the reaction is complete, cool down and add water to stop the reaction. Products with CH 2 Cl 2 Extraction, washing the organic phase with brine, anhydrous MgSO 4 It was dried, concentrated by rotary evaporation to remove the solvent, and 1.13 g of light yellow solid 1 was obtained by column chromatography with ethyl acetate and petroleum ether. 1 H NMR (CDCl 3 ,400MHz):δ7.18-7.26(m,10H),7.27-7.30(m,4H),7.37-7.51(m,4H),7.60-7.68(m,4H),7.78-7.82(d,J= 8.8Hz, 4H).

Embodiment 2

[0034] Example 2: Synthesis of fluorinated 9,9'-bianthracene blue light material 5:

[0035]

[0036] Under nitrogen atmosphere, to 30mL THF and 10mL, 2.0mol·L –1 K 2 CO 3 In the solution, 10,10′-dibromo-9,9′-bianthracene (2.34mmol), 2,4-difluorophenylboronic acid (8mmol) and Pd(PPh 3 ) 4 (0.35 mmol). After the reaction, the mixture was heated to reflux for 24h, and the reaction was tracked by point plate. After the reaction is complete, cool down and add water to stop the reaction. Products with CH 2 Cl 2 Extraction, washing the organic phase with brine, anhydrous MgSO 4 It was dried, concentrated by rotary evaporation to remove the solvent, and 1.22 g of light yellow solid 5 was obtained by column chromatography with ethyl acetate and petroleum ether. 1 H NMR (CDCl 3 ,400MHz): δ7.17-7.23(m,12H),7.38-7.41(m,4H),7.53-7.61(q,4H),7.74-7.61(d,J=8.0Hz,4H).

Embodiment 3

[0037] Example 3: Synthesis of fluorinated 9,9'-bianthracene blue light material 13:

[0038]

[0039] Under nitrogen atmosphere, to 30mL THF and 10mL, 2.0mol·L –1 K 2 CO 3 In the solution, 10,10′-dibromo-9,9′-bianthracene (2.34mmol), 2,3,4tri-fluorophenylboronic acid (8mmol) and Pd(PPh 3 ) 4 (0.35 mmol). After the reaction, the mixture was heated to reflux for 24h, and the reaction was tracked by point plate. After the reaction is complete, cool down and add water to stop the reaction. Products with CH 2 Cl 2 Extraction, washing the organic phase with brine, anhydrous MgSO 4 It was dried, concentrated by rotary evaporation to remove the solvent, and 1.38 g of white solid 13 was obtained by column chromatography with ethyl acetate and petroleum ether. 1 H NMR (CDCl 3 ,400MHz): δ7.18-7.20(m,8H),7.27-7.31(t,4H),7.38-7.43(m,4H),7.73-7.78(d,J=8.8Hz,4H).

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Abstract

The invention discloses a fluorine-substituted 9,9'-dianthracene blue light emitting host material and its application. The position and the number of a peripheral strong electrophilic group fluoro or trifluoromethyl are changed to realize a high fluorescence quantum efficiency and a good luminescence peak blue shift, and realize dark blue light emission by cooperating with an appropriate host (CBP); and the position and the number of the peripheral strong electrophilic group fluoro or trifluoromethyl are changed to make the material have an appropriate highest occupied molecular orbital and a lowest unoccupied orbital energy and realize good overlapping of the emission spectrum and the absorption spectrum of an object DPAVBi, so energy can be effectively absorbed and transferred to the object, thereby the luminescence of the object is caused, and the performances of a device are improved. The material has the advantages of good heat stability, good luminescence performance, easy synthesis and convenient purification, and can be widely used in the fields of organic field effect transistors, organic electroluminescent devices, the organic lasers and organic photovoltaic solar batteries.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric functional materials, and relates to a blue light host material, in particular to a fluorine-substituted 9,9'-bianthracene blue light host material and its application. Background technique [0002] Organic electroluminescent devices have the advantages of high luminous efficiency, low driving voltage, active luminescence, high brightness, wide viewing angle, fast response, and full-color flat-panel display, so they have broad application prospects in the field of flat-panel displays and solid-state light sources. . Since C.W.Tang et al. of Kodak Company first developed a valuable low driving voltage organic electroluminescent device in 1987, OLEDs have attracted great attention of scientific researchers from all over the world and become a research hotspot in the field of display today. In the research of OLEDs, red, green, and blue primary color materials are the basis for full-co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07C25/22C07C17/263H01L51/54H01L51/46
CPCY02E10/549
Inventor 吴朝新李战锋焦博于跃侯洵
Owner 西安极光新材料科技有限公司
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